Forging Your Own Path with Kris Jennings

Can you build a six to seven figure Soloist business doing the opposite of what “the experts” recommend? Consultant Kris Jennings has created exactly that by forging her own path:

How her “tiny, tiny” email list delivered over $1 million in revenue (and provides a vehicle to nurture key referral relationships).

How she thinks about and serves her list (hint: it’s exactly the opposite of what most every email marketer recommends).

What she does with advice from experts and “gurus”.

How she measures success—and how her metrics have changed as her business matures.

The evolution of her risk-taking philosophy in business—and what elements must be present for her to say an unqualified “yes”.

LINKS

Kris Jennings Website | LinkedIn

Rochelle Moulton Email List | LinkedIn | Twitter | Instagram

BIO

With nearly thirty years of experience, Kris Jennings’ work has helped more than a million people change. From large technology implementations to digital products for Type 2 diabetes, she designs ways to help people take small steps forward.

She has run a consulting and advisory business since 2012 and her clients include Fortune 100 global organizations. She now primarily supports change leaders and project teams. Her first book will be released this fall (2024).

She holds a bachelor's degree from The Medill School of Journalism at Northwestern University. 

Kris and her husband live in Minneapolis, Minnesota with their two delightfully curious, mischievous kittens. She dedicates time each year to bucket list adventure travel with their two young adult sons.

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RESOURCES FOR SOLOISTS

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The Soloist Women community: a place to connect with like-minded women (and join a channel dedicated to your revenue level).

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TRANSCRIPT

00:00 - 00:11

Kris Jennings: To me, it's not about selling something. It's about reaffirming the relationship that I have with those past clients, because they're gonna be the ones that are gonna refer me to other business. And I'm

00:11 - 00:16

: gonna be the 1 that's gonna refer me to other business. And I'm gonna be the 1 that's gonna refer me to other business. And I'm gonna be the 1 that's gonna refer me to other business.

00:16 - 00:56

Rochelle Moulton: Hello, hello. Welcome to the Soloist Life podcast where we're all about turning your expertise into wealth and impact. I'm Rochelle Moulton and today I'm here with consultant Chris Jennings, whose work has helped more than a million people change From large technology implementations to digital products for type 2 diabetes, she designs ways to help people take small steps forward. Chris has run a consulting and advisory business since 2012, and her clients include Fortune 100 global organizations. She now primarily supports change leaders and project teams and her first book will be released this fall. Chris, welcome.

00:56 - 00:58

Kris Jennings: Thanks, Rochelle, it's great to be here.

00:59 - 01:31

Rochelle Moulton: Well, we've had quite an exchange of ideas and conversation about growing a soloist business. In fact, you introduced me to earlier guest Heather Welpley a while back. But the initial spark was when you dropped just this very casual comment about your, and I quote, tiny, tiny email list generating over a million dollars in revenue for you so I'm kind of thinking we should start there but let's go back just a little bit so you started your firm in 2012. Tell us how that happened How did that

01:31 - 02:10

Kris Jennings: come about? So it's not the great story of like being excited and leaving the big organization to pursue my dream as a solo opener. It's actually quite the opposite. I was laid off. A very surprising layoff from an organization that had never done layoffs at the end of the recession, just coming out of that span from 2008 to 2012. So it was January of 2012 and got the layoff notice and within 2 weeks actually had a consulting gig. So it wasn't the route I was planning to take, but a friend nudged me towards trying it out.

02:11 - 02:19

Kris Jennings: And honestly that set me on the path to where I am today, which is 12 years later, having done some amazing projects with some amazing teams.

02:20 - 02:27

Rochelle Moulton: I love that turning lemons into lemonade. So how long did it take you to earn your first hundred thousand? Do you remember?

02:28 - 02:44

Kris Jennings: It was that first year. So I am 1 of those unusual people that my skill set is highly in demand and I have never had a break. So for 12 years, it's been go, go, go. And that's been financially rewarding.

02:44 - 03:06

Rochelle Moulton: Yeah. I'm hearing an undercurrent in there, which we'll get to. So you know I have to ask you more about your tiny, tiny list. I mean, it feels like there are lots of people in our space shouting that building a giant list is the way to go. But we know when you're in a high-end B2B consulting space, the metrics tend to look different. So, like, who's on your list?

03:06 - 03:37

Kris Jennings: I mean, how tiny is tiny? Tiny is under 100 people. I love that. Yeah, really, right? So stop and think about that. And I've been writing it for a year. So I've been diligently writing for about a year. So I was 11 years into my entrepreneurial journey before I really kind of did any kind of what I would say outreach or any kind of marketing. Literally, my business has been 100% referral based. So I've always gone from, you know, 1, if you will, friend to another, people who are behind the scenes saying, okay, we have the,

03:37 - 04:12

Kris Jennings: we're doing the same thing you guys did. Can you please recommend somebody? And that's how I've, I've really pieced together a magical career over the last 12 years as a solopreneur. So I started writing the newsletter every week because I'm a writer at heart. My background and my degree is in journalism and I love telling stories and I have ghostwritten for executives and it's still a big part of what I do in my work in change. But it was really about me and writing for me. And so the newsletter has become this thing of like, I

04:12 - 04:47

Kris Jennings: just really share it within the close circle of people who've worked with me and family and friends who are, who know I'm very passionate about change and it is a very safe space for me and actually all of us on the list to collaborate. So it's not the traditional email newsletter. It's the, hey, we're going to try and experiment this month. We're going to do some change experiments. I do whatever I want because I know that the people on the list are reading it. And I just looked at the open rate and prep for this. So

04:47 - 04:52

Kris Jennings: my open rate is hovers between 70 and 80%. This week it was 82%.

04:52 - 05:09

Rochelle Moulton: So anybody listening to that just had pangs of jealousy at that open rate. That's unusually high. But I also think the way you described it is really interesting. It feels like a collaborative space versus a one-way speaking space. Yeah. I mean, I think 1

05:09 - 05:43

Kris Jennings: of the things that kind of who I am is like, let me create something and play with it and see what happens. So with the list, it's like, I think the mainstream thinking on it is build your list, build your list, because then you're gonna sell something to everybody who's on your list. Mine's the opposite. I've already sold, as you said, I've already sold a million dollars worth of services to the people on that list. So to me, it's not about selling something, it's about reaffirming the relationship that I have with those past clients, because they're

05:43 - 06:09

Kris Jennings: going to be the ones that are going to refer me to other business. But just more so from this like, yeah, it doesn't have to be about monetizing the list. It can actually be the reverse, right? I've already done that. And now here's this place where we get to cultivate and strengthen the relationship that we've built through doing hard projects together. Well, and I like the spirit of generosity that kind of weaves through the

06:09 - 06:27

Rochelle Moulton: way you describe that, right? Like, I've helped you, you've helped me with the financial exchange, and let's continue to be able to grow together. You know, something that you said, and I was thinking about it, conversation we had 1 time about your book. So did you start writing for the list at the same time you started writing

06:27 - 07:01

Kris Jennings: your book? Like, did 1 make you do the other? Or how were they connected, or if at all? I started doing the newsletter first and it was probably 6 months in that I formally like started the book manuscript. There's definitely overlap and I think anybody who hasn't done a lot of, you know, marketing for themselves and they're in their solopreneur business, it's like, you know, a newsletter is a great place to get your thoughts on paper and say practice or have some content for something that you might do later, such as a book. So for me,

07:01 - 07:20

Kris Jennings: it's been also a way to get feedback, right? So I know the points that I've made in the newsletter and I know those content areas where it's like, wow, I had great feedback, you know, that prompted 2 or 3 comments, you know, back. And that's allowed me to kind of like, hey, I'm going to go deeper on that content in the book.

07:21 - 07:35

Rochelle Moulton: I love this. It's just counterintuitive. So what do you tell yourself when you get advice or you read advice from, you know, experts to do some kind of marketing gymnastics to grow your lists? Like what goes through your head?

07:35 - 08:07

Kris Jennings: I mean, 1 thing I've learned as a solopreneur is like, it's really hard not to do comparisonitis. It's really hard to say follow people and think, oh, I wanna learn from them, right? I wanna mimic what they're doing. But it is actually a moment of like, I'm going to learn what they're doing, and then I'm going to apply it to myself. I'm going to decide whether or not it works for me. Does this feel like it's right for who I am, my voice, my business, where I'm at and how I wanna grow my business, the types

08:07 - 08:38

Kris Jennings: of work I wanna do, who I wanna call in? There's a lot of shoulds out there in marketing and I definitely feel like you've gotta really have some blinders on in terms of learning, but then actually applying it to yourself and being willing to say, you know what? I like that idea, but it doesn't work quite right for me. And the only way to do that is to play. So I've given myself a lot of permission to fail, to try things and to not expect any wild success, but just to see what am I going to

08:38 - 08:39

Kris Jennings: learn from it.

08:39 - 09:10

Rochelle Moulton: I think we've all interacted with people who are doing whatever their latest guru has advised them to do. And, okay, this time I'm going to do this and it doesn't work, or this time I'm going to do that and it doesn't work. Not necessarily because it was a bad tactic, but because it didn't apply, or the person didn't take the time to figure out how to do what you said, which is adjust it for where you're going, for your style. And I think we can push ourselves out of our comfort zones. I think that's a good

09:10 - 09:46

Rochelle Moulton: thing. But we also want to take a decent bet, right? Something that we think is scary, but feels like something we would want. Like the outcome is something we would want and then we'll try it. But yeah, it is, it's a process. So I'm just curious, do you see or feel a downside with a small list? I mean, just as an example, it would be challenging to say, pivot from these huge consulting projects to something more retail, like $5, 000 workshops. So do you ever think about the size of the list and where you want to

09:46 - 09:47

Rochelle Moulton: take that in the future?

09:47 - 10:22

Kris Jennings: In the last couple of years, I think things have changed. I think the consumers, and I say consumers, meaning we're all consumers, right, of other people's content and purchasers of products, et cetera, I think we're more sophisticated and we're perhaps a little more cynical about the stuff that we get, including from email lists. So there's a variety of ways that we think about purchases, and that means anything from people seeing me on LinkedIn, people hearing me on this podcast, people picking up my book, people seeing it on Amazon, people getting a referral from it, somebody giving

10:22 - 10:50

Kris Jennings: my book to someone else. So there's a variety of ways that I think marketing can work. And I don't necessarily think that the lists as they once were used to be the end all be all. I think there's so much fragmentation and just in terms of marketing and what's being thrown at any of us at any given time, that it's like you can't rely on just 1. You've got to really think about the whole system and how you're getting your message out to your audience.

10:50 - 11:20

Rochelle Moulton: Yeah, well plus I also think your book, which we haven't talked about, is the kind of book where you don't have to sell a gazillion copies. You have the kind of book just like your list where you could sell 10 copies if they were to the right people, right? And I'm assuming your book is going to be pretty highly focused and targeted to your ideal audience. And so I just love the conventional wisdom would say, I'm going to sell a thousand copies in the first 2 days, and I've got to get to 10, 000 copies. And

11:20 - 11:34

Rochelle Moulton: when you have a business model like yours, that's not the metric that matters. I mean, it feels good. It would be nice to be on the New York Times bestseller list, but it isn't necessary to be able to serve the purpose that you wrote the book for.

11:35 - 12:09

Kris Jennings: Yeah, I think that's very, that's very astute in terms of like, why am I writing the book? And honestly, it was quite challenging in terms of working with the editor team that I did, because it was not really something they'd really ever considered, right? That I would have a very small audience, a very niche audience from my book. And that even how I would get it into the hands of the people who would use it would be extremely targeted in thinking about the intermediaries that are likely to be the repeat, if you will, distributors of my

12:09 - 12:34

Kris Jennings: books. So in my world, that looks like project managers, that looks like PMO offices, project management offices, sorry for the lingo, the jargon, or system implementers, right? Those people who are regularly doing large-scale projects and might not have a skillset like mine within a given project or within a given client team. So I've really strategically thought about how am I

12:34 - 13:08

Rochelle Moulton: going to partner with those folks to make sure that they have my book and that it becomes this business card that they're handing out on my behalf for at least several more years, at least until I write the next 1. Well, you bring up a great point, and I've seen this with some clients where their book was so targeted to a niche, and literally they could repay all of the time and money that they spent on their book with 1 single client, right, that came from that book. And a lot of editors, like they don't get

13:08 - 13:29

Rochelle Moulton: that. And in fact, they can try to edit your book for a larger market. And they just like, they can't help themselves because that's what they're used to. That's what everybody wants is to have a bigger market. So thank you for sharing that. It's something you really have to watch out for and it helps to find an editor who totally gets it. But sometimes it takes a round or 2. Yeah, and

13:29 - 13:36

Kris Jennings: it's definitely 1 of the reasons I self-published to be able to have that ultimate control over that creativity. Yeah.

13:36 - 13:55

Rochelle Moulton: So the theme I hear loud and clear from you, whenever we've chatted, is to forge your own path. So how do you measure your success? Are you using monthly, quarterly, annual metrics? What's your process to assess your progress with your business in your life?

13:56 - 14:31

Kris Jennings: Oh that's a great question. For me, if I had had answered that 12 years ago, it probably would be how do my financials look, right? And, you know, what do I have in the queue for the next quarter? And actually, most of my work goes much longer than that. So most of my projects are, you know, 12 to 18 months. So my time cycles, you know, are very, very, very long. And now I'm really thinking differently about what time of year is it? We're coming up on summer in Minnesota. Right. And So for me, I think,

14:31 - 15:06

Kris Jennings: wow, I want to make sure I have the least amount of stuff on my plate right now so that I can enjoy the short summer that we have here and I get to swim outside and I get to go to breakfast with my 22 year old, my youngest son who will be home from college for the summer. So for me, it's much more measures of life satisfaction and just where does the business fit into my life within a year? And giving myself a lot more flexibility with, you know, and if you will, ups and downs...